Oxidative Kinetic Resolution of Some Naphtholic Alcohols Mediated by a Chiral Hypervalent Iodine Reagent

Abstract

A chiral aryl iodide enables the catalytic, oxidative kinetic resolution of various 2-[(3-hydroxy-2-alkyl)propyl]naphthalen-1-ols.

Key words

alcohols - asymmetric catalysis - hypervalent iodine - kinetic resolution

• References

• 1 Jain N. Xu S. Ciufolini MA. Chem. Eur. J. 2017; 23: 4542

General reviews on hypervalent iodine chemistry:
• 2a Yoshimura A. Zhdankin VV. Chem. Rev. 2016; 116: 3328
• 2b Wirth T. Hypervalent Iodine Chemistry . Springer-Verlag; Berlin: 2016
• 2c Zhdankin VV. Hypervalent Iodine Chemistry . Wiley; Chichester: 2014
• 3 For an excellent bibliography of chiral iodides as promoters of enantioselective reactions see: Fujita M. Heterocycles 2018; 96: 563 ; and literature cited therein
• 4a Uyanik M. Yasui T. Ishihara K. Angew. Chem. Int. Ed. 2010; 49: 2175
• 4b Uyanik M. Yasui T. Ishihara K. Angew. Chem. Int. Ed. 2013; 52: 9215
• 4c Uyanik M. Yasui T. Ishihara K. J. Org. Chem. 2017; 82: 11946
• 5a Beesley RM. Ingold CK. Thorpe JF. J. Chem. Soc., Trans. 1915; 107: 1080
• 5b Bachrach SM. J. Org. Chem. 2008; 73: 2466
• 6 This would be an example of oxidative kinetic resolution; for review, see: Keith JM. Larrow JF. Jacobsen EN. Adv. Synth. Catal. 2001; 343: 5 ; (see esp. 11 ff)

To illustrate:
• 7a Oxidative kinetic resolution of rac-1-phenylethanol: Zhdankin VV. Koposov AY. Netzel BC. Yashin NV. Rempel BP. Ferguson MJ. Tykwinski RR. Angew. Chem. Int. Ed. 2003; 42: 2194 ; (see especially p 2195, paragraph above Table 1)
• 7b Oxidative kinetic resolution of rac-1-(2-naphthyl)ethanol and meso-1,2-diphenylethane-1,2-diol: Ladziata U. Carlson J. Zhdankin VV. Tetrahedon Lett. 2006; 47: 6301
• 7c Kinetic resolution of a secondary homoallyl alcohol via oxidative lactonization: Fujita M. Mori K. Shimogaki M. Sugimura T. Org. Lett. 2012; 14: 1294
• 7d We thank the referees for bringing the above literature to our attention.
• 8 See Supporting Information for relevant synthetic, chemical, and spectroscopic data, and other characterization details.
• 9 Fluoroalcohols such as CF₃CH₂OH and (CF₃)₂CHOH are privileged media for the conduct of many reactions mediated by hypervalent iodine species: Dohi T. Yamaoka N. Kita Y. Tetrahedron 2010; 66: 5775
• 10a Terakado D. Koutaka H. Oriyama T. Tetrahedron: Asymmetry 2005; 16: 1157
• 10b Sakai T. Kishimoto T. Tanaka Y. Ema T. Utaka M. Tetrahedron Lett. 1998; 39: 7881
• 10c Ghanemi A. Aboul-enein HY. Chirality 2005; 17: 1
• 10d Strübing D. Krumlinde P. Piera J. Bäckvall J.-E. Adv. Synth. Catal. 2007; 349: 1577
• 11 Racemic 1n is a known compound: Kongkathip N. Kongkathip B. Siripong P. Sangma C. Luangkamin S. Niyomdecha M. Pattanapa S. Piyaviriyagul S. Kongsaeree P. Bioorg. Med. Chem. 2003; 11: 3179